The present invention relates to a series of new phenoxyalkylaminopyrimidine derivtives which have valuable insecticidal and acaricidal activities and also provides processes for preparing these derivatives and compositions containing them as the active ingredient.
Insects and acarids cause considerable damage to plants and can represent a serious danger to health; at best, they are a major nuisance. Accordingly, large sums are spent to destroy or deter them. Although many insecticides and acaricides are available, a large number of these have to be used with care, because they can endanger animals or because of their phytotocicity. Moreover, because insects and acarids have short life cycles, they can develop immunity to many of the commonly used insecticides and acaricides, and, accordingly, there is always a continuing need for new compounds exhibiting insecticidal and acaricidal properties.
A number of phenoxyalkylamine derivatives is known, e.g. from U.S. Pat. Nos. 4,213,987, 4,435,402 and 4,562,193. These known compounds can, broadly speaking, be represented by the formula: ##STR2## in which: R.sup.a and R.sup.b each represent alkyl groups;
R.sup.c represents an alkylene group; and PA1 Het represents a heterocyclic ring system, for example a pyrimidine ring or a pyrimidine ring fused to another ring, e.g. fused to a benzene ring (to form a quinazoline ring) or fused to a cycloalkane or thiophene ring, and, of course, such rings are optionally substituted. PA1 R.sup.2 and R.sup.3 are independently selected from the group consisting of C.sub.1 -C.sub.4 alkyl groups, halogen atoms, C.sub.2 -C.sub.4 alkoxyalkyl groups, C.sub.2 -C.sub.4 alkylthioalkyl groups and C.sub.3 and C.sub.4 cycloalkyl groups, or R.sup.2 and R.sup.3 together represent, with the carbon atoms to which they are attached, a 5- or 6-membered ring which is a carbocyclic ring or is a heterocyclic ring containing a single oxygen or sulfur hetero-atom, the ring being unsubstituted or having 1 or 2 substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl groups and halogen atoms; PA1 m is 2 or 3; PA1 R.sup.4 and R.sup.5 are independently selected from the group consisting of hydrogen atoms, C.sub.1 -C.sub.4 alkyl groups and halogen atoms; and PA1 R.sup.6 represents a group of formula --A--B--(DO).sub.n --E, where PA1 or a group of formula --CH.sub.2 --W, where: PA1 Z' represents a group of formula &gt;CH.sub.2 or &gt;S.fwdarw.(O).sub.s, in which s is 0, 1 or 2; PA1 Q represents an alkylene or alkenylene group having from 2 to 5 carbon atoms, for example an ethylene, trimethylene, tetramethylene, pentamethylene, vinylene, propenylene, 1-butenylene or 2-butenylene group; PA1 R.sup.8 represents a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, for example a methyl, ethyl, propyl or butyl group, preferably a hydrogen atom or a methyl group; PA1 R.sup.9 represents a C.sub.1 -C.sub.4 alkyl group (e.g. as exemplified above in relation to R.sup.1, and preferably a methyl, ethyl or propyl group), a C.sub.1 -C.sub.4 haloalkyl group (e.g. a chloromethyl, bromomethyl, fluoromethyl, iodomethyl, dichloromethyl, trifluoromethyl, 2-chloroethyl, 2,2-dichloroethyl, pentabromoethyl, 3-fluoropropyl or 2,3-dibromobutyl group, preferably a halomethyl group) or a phenyl grouup; and PA1 r is 0, 1 or 2. PA1 Q represents an alkylene or alkenylene group having from 2 to 5 carbon atoms; PA1 R.sup.8 represents a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group; PA1 R.sup.9 represents a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group or a phenyl group; PA1 r is 0, 1 or 2; PA1 Z" represents a group of formula &gt;CH.sub.2 or &gt;S.fwdarw.(O).sub.s ; and PA1 s is 0, 1 or 2. PA1 R.sup.1 represents a hydrogen atom or a methyl group; PA1 one of R.sup.2 and R.sup.3 represents a methyl or ethyl group and the other represents a methyl group, an ethyl group, a chlorine atom or a bromine atom, or R.sup.2 and R.sup.3 together from a cyclopentene, cyclohexene, benzene or thiophene ring fused to the pyrimidine ring, said rings being unsubstituted or said cyclopentene, cyclohexene and benzene rings having one or two substituents selected from the group consisting of methyl, chlorine and fluorine substituents or said thiophene ring having one or two methyl substituents; PA1 m is 2; PA1 R.sup.4 represents a hydrogen atom, a methyl group or an ethyl group, preferably a methyl group; PA1 R.sup.5 represents a hydrogen atom, a chlorine atom or a methyl group, preferably a hydrogen atom or a methyl group; PA1 A represents a C.sub.1 -C.sub.5 alkylene group or a C.sub.1 -C.sub.5 alkylene group having a single methoxy substituent, preferably a C.sub.1 -C.sub.5 alkylene group; PA1 --B--(DO).sub.n -- represents an oxygen atom, a sulfur atom, an imino group or a group of formula --NH--(CH.sub.2).sub.2 --O--, --O--(CH.sub.2).sub.p --O-- or --O(CH.sub.2).sub.q --O--(CH.sub.2).sub.q --O-- (in which p is an integer from 1 to 3 and q is 1 or 2), preferably said oxygen atom or a group of formula --O--(CH.sub.2).sub.p --O-- or --O--(CH.sub.2).sub.q --O--(CH.sub.2).sub.2 --O-- (in which p and q are as defined above). PA1 R.sup.1 represents a hydrogen atom or a methyl group; PA1 one of R.sup.2 and R.sup.3 represents a methyl or ethyl group and the other represents a chlorine atom or a bromine atom, or R.sup.2 and R.sup.3 form a benzene or thiophene ring fused with the pyrimidine ring; PA1 R.sup.4 represents a methyl group; PA1 R.sup.5 represents a hydrogen atom; and PA1 R.sup.6 represents a group of formula --CH.sub.2 --CH.dbd.N--OR.sup.7, in which R.sup.7 represents an ethyl group or an allyl group. PA1 R.sup.1 -R.sup.5 are as defined in (13) above; and PA1 R.sup.6 represents a group of formula --CH.sub.2 --W in which W represents a group of formula ##STR8## in which Z, Z', Z" and Q are as defined in (11) above, R.sup.8 represents a hydrogen atom or a methyl group, R.sup.9 represents a methyl group, an ethyl group or a chloromethyl group and r is 0, 1 or 2. PA1 All--allyl PA1 Bu--butyl PA1 Bz--benzyl PA1 Dit--1,3-dithiolan-2-yl PA1 Dix--1,3-dioxolanyl PA1 (2-Dix--1,3-dioxolan-2-yl PA1 4-Dix--1,3-dioxolan-4-yl etc.) PA1 Dot--1,3,2-dioxathiolan-4-yl PA1 Et--ethyl PA1 Mal--methallyl PA1 Me--methyl PA1 Mor--morpholino PA1 Otl--1,3-oxathiolan-2-yl PA1 Ph--phenyl PA1 Pn--pentyl PA1 Pr--propyl PA1 cPr--cyclopropyl PA1 iPr--isopropyl PA1 Prg--propargyl (=2-propynyl)
Such compounds have insecticidal and acaricidal activities and are effective for the eradication of various noxious insects and mites which are problems in agriculture or horticulture, for example the diamondback moth (Plutellae xylostella), aphids, the two-spotted spider mite (Tetranychus urticae) and the citrus red mite (Panonychus citri).
We have now found that a class of compounds similar to the known ones described above, but which have a highly specific class of substituted alkyl groups at the 4-position of the phenyl group in the formula shown above, have insecticidal and acaricidal activities far superior to those of the known compounds, and, in particular, they have superb acaricidal activity.